Thiophene → (+/-)-Methyl 1-(4-aminophenyl)-alpha-phenyl-4-piperidineacetate

HRID 852453Notes

Reaction equation

HRID 852453 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([CH:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:17]([O:19][CH3:20])=[O:18])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.S1C=CC=C1.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([CH:16]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:17]([O:19][CH3:20])=[O:18])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 22499408(+/-)-Methyl 1-(4-nitrophenyl)-alpha-phenyl-4-piperidineacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 22499374(+/-)-Methyl 1-(4-aminophenyl)-alpha-phenyl-4-piperidineacetateYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of intermediate (14) (0.0022 mole) in methanol (100 ml) was hydrogenated at 50° C. with palladium-on-carbon (10%) (0.1 g) as a catalyst in the presence of a 4% thiophene solution (0.1 ml). After uptake of hydrogen (3 equivalents), the catalyst was filtered off and the filtrate was evaporated. The residue was triturated in hexane. The precipitate was filtered off and dried, yielding 0.7 g of (±)-methyl 1-(4-aminophenyl)-α-phenyl-4-piperidineacetate (intermediate 15, melting point 125° C.).

Workup

  1. customthe filtrate was evaporated
  2. customThe residue was triturated in hexane
  3. filtrationThe precipitate was filtered off
  4. customdried

Sources & evidence

ORD record
ord-3b4a9062767d496b8a2e96c5abe8c3ff
Source dataset
uspto-grants-2007_08
Patent number
US07253157B2

Reaction notes

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